Trimethylsilyl cyanide → HCID 22175979, compound

Participants

Reaction Steps

To a mixture of (3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl)methyl methanesulfonate (39 g, 0.75 mmol) in acetonitrile (5 mL) and tetrahydrofuran (4 mL) were added trimethylsilyl cyanide (0.15 mL, 1.1 mmol) and a solution of 1.0 M tetrabutylammonium fluoride: in tetrahydrofuran (1.1 mL), and then the mixture was stirred at 80° C. for 30 min. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2 (v/v)) to give tert-butyl[6-(cyanomethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.25 g, 75%) as a colorless oil.

Provenance & Evidence